


An (Almost) Failed Arrangement

by ArgentsArrows



Series: Halechester Fics [1]
Category: Supernatural, Teen Wolf (TV)
Genre: A/B/O, Alpha!Dean, Arranged Marriage, M/M, Multi, Omega!Derek, Sorry I don't write smut, age gap, all soft here boys, almost cheating? but not quite dean does not cheat, cas and dean have moments but they aren't going to be romantic in this fic, derek is 23 and dean is in his early 30s, honestly derek and dean need hugs, if that wasnt obvious, long awaited rewrite because you dont deserve 2018 writing, past Kate/Derek, past dean/cas, traditional family meets "ew tradition" family, with some angst
Language: English
Status: In-Progress
Published: 2020-10-13
Updated: 2020-10-13
Packaged: 2021-03-07 22:40:57
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,085
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26985334
Author URL: https://archiveofourown.org/users/ArgentsArrows/pseuds/ArgentsArrows
Summary: The Hales had always been an extremely traditional family. When their Omegas finished their first heat, they immediately began training to be the perfect spouse. When their Alphas finished their first rut, they were taught to be the perfect Alpha and how to keep their Omega in line. As soon as training his finished, the parents work to arrange a marriage between their child and a suitable Alpha/Omega. They aren’t strict with their Betas, only deciding what career they go into and paying for their education.The Winchesters are much more lenient when it comes to tradition. They don’t force their Alphas, or their Omegas, to undergo training to be the “perfect spouse”. They don’t think it exists, and they’ve made that clear. But when Talia Hale, a very wealthy and well-known Alpha, approaches Mary Winchester about arranging a marriage between her Omega son and one of the Winchester Alphas; who are they to say no?Their sons do have somewhat of a say in the matter; whether they wish to meet before the wedding or not. They agree to meet, to see what they’re getting themselves into. Dean decides to break Derek's submissive behavior, but it's harder than he'd expected.
Relationships: Castiel/Dean Winchester, Derek Hale/Dean Winchester, Jessica Moore/Sam Winchester, Laura Hale/OMC
Series: Halechester Fics [1]
Series URL: https://archiveofourown.org/series/1969450
Comments: 5
Kudos: 8





	An (Almost) Failed Arrangement

**Author's Note:**

> The long awaited rewrite of The Arrangement!  
> Thank you to everyone that commented and read, I never thought that fic would actually get any attention, and that means a LOT to me! As always, I'm open to suggestions and will gladly answer questions on the story; hope you enjoy!

Mary Winchester was, safe to say, overwhelmed with worry. Her youngest son, Samuel, was finishing his second year of law school and expecting a darling child with his girlfriend of three years, Jessica Moore. With him usually away or busy studying for whatever tests he was taking in his forever time-consuming classes, Jessica had taken to spending quite a bit of time at the Winchester household. Mary didn't mind, of course--no, she loved having the young woman around--but she couldn't help but wonder when it would end. When Sam graduates, will he suddenly take her away and move into a home of their own? It was expected that he wouldn't want to share his "territory" with his father forever, but just how long did she have left to hold her little boy in the nest?

Her eldest, on the other hand, was a completely different story; she couldn't wait for him to spread his wings and move on to a life of his own. He had his own apartment downtown, of course; it'd be quite the issue with John if he didn't at his age. But, he still worked at the family business. The restaurant was near and dear to his parents, but it was clear Dean didn't hold the same love for the business; he wanted to run a garage, fix cars. But, he just didn't have the money, and he wouldn't make that off of a waiter's wage, even with his parents running the restaurant.

The Devil's Trap wasn't even doing that well anymore! Staff were harder to come by, and the decor was simply outdated, but she and John couldn't afford anything better. She'd voiced her distaste with the layout several times, and always got the same answer; "We don't have the money, Mary." What if they never got-

A quiet _ping_ on her phone, accompanied by the vibration against the counter as it buzzes, pulls Mary out of her worries. It was a number she didn't recognize, but the name signing the end of the text was one that she'd never forget; _Talia Hale_.

oOoOoOoOoOoOoOoOoOoOoOoOoOoOoOoOoOoOoOoOoO

The message was received two days ago, and she has yet to give Talia an answer. She’d have to discuss the matter with John, and Dean – her only unmated son. The two were currently working their shifts at the restaurant and had been busy or exhausted when she’d went to discuss the matter with them the day before.

While she waits for them to finish her shift, Mary busies herself with the dishes at home. Jessica had offered to get them out of the way but was quickly dismissed because Mary insisted she needed to relax to prevent stressing out herself or the baby. As a Beta, it’d been rather hard for Jessica to get pregnant in the first place, and so Mary was extra strict on what she could and couldn’t do.

Mary was finishing up the dishes when Jessica’s voice called out to her. “Mary, the boys are home.”

“Sam too?” She questions, turning off the sink and drying her hands before heading out to join the other woman in the living room.

“Not yet, no,” Jessica responds, shaking her head before turning her attention back to what she was watching on the TV.

Dean and John enter the house mutely, leaving their shoes near the door as they’d been told repeatedly to do. “You said you had to talk to us,” John calls out, heading toward the sounds of Jessica and Mary talking.

“Right. Yes, we need to talk,” Mary confirms, looking up from where she’s now sitting near the younger woman, “Please sit down.” The men nod, sitting down in the recliners.

“Talia Hale reached out to me,” She begins, immediately having the attention of her husband.

“High school Talia?” He questions, earning a nod from his wife.

“She wants to arrange something between Dean and her son,” she begins, catching the attention of Dean.

“I thought we didn’t do that,” Dean interrupts, scowling at his mother, “You told me I wasn’t going to be forced to follow tradition.”

“And you won’t be,” Mary reassures, “This is completely your decision. It’s why I wanted you to be here when I mentioned it to your father.” Hesitating, Dean goes silent and nods.

The discussion goes on for around half an hour, with Mary explaining to Dean who Talia is and what’s expected of him if he agrees. John also chooses to mention the benefits it would bring the family, earning looks of disapproval from his mate; it wasn’t that she didn’t appreciate him trying to help, she just didn’t want Dean making the decision purely to benefit them.

oOoOoOoOoOoOoOoOoOoOoOoOoOoOoOoOoOoOoOoOoO

Dean heads to bed that night with a lot on his mind. He’d agreed to let his mother arrange the marriage between him and Talia’s son, be he couldn’t stop thinking about the possibilities of what could happen. From what he was told about his mystery fiancé, he was twelve years the Omega’s senior. Age gaps like that weren’t new, they happen rather often in situations like this one, but he couldn’t help but think about how weird things might be.

What if the Omega is too immature to take things seriously? What if he doesn’t like Dean because he’s so much older? Would what he wants matter like it did with Dean? Did he even _want_ to marry Dean? Those thoughts and so many others occupy his mind as he lies in bed, his hands folded over his stomach and blank stare locked on the ceiling. His lower lip is held between his teeth, a habit of his for when he has nothing to chew on; a sign that he’s anxious. Dean was certain he was overthinking, that everything would be fine, and he was worried over nothing. But he didn’t know for sure. How could he? He just agreed to getting engaged to a man he’d never met; a man that he knows little to nothing about.

He doesn’t let himself think about it any longer, rolling over onto his side and getting comfortable. He knew he’d have a tough time going to sleep because of the day’s events, but he could try. His mother had promised to respond to Talia, and now he just needed to know if his new fiancé – hell, he didn’t even know the man’s name yet – would agree to meet him before their wedding day. With that being his final conscious thought, Dean drifts off.

**Author's Note:**

> I'll admit, I copy and pasted the last two sections with minor edits aside from spacing and making it easier to read. This is just a brief introduction, and the next chapter will go more in depth; the deal, the reason behind the sudden deal, and we'll see more about Dean's thought process, and how he feels about this.


End file.
